The progress in telemedicine can be observed globally and locally. Technological changes in telecommunications systems are intertwined with developments in telemedicine. The recent COVID-19 pandemic has expanded the potential of teleconsultations and telediagnosis solutions in all areas of medicine. This article presents: (1) an overview of milestones in the development of telecommunications systems that allow progress in telemedicine and (2) an analysis of the experiences of the last seven conferences of telemedicine and eHealth in Poland. The telemedicine and eHealth conferences have grown steadily in Poland since their inception in the late 1990s. An exemplary conference program content was used to assess the scientific maturity of the conference, measured by the indices of research dissemination and the impact of publications. The overview presents progress in selected areas of telemedicine, looking at local developments and broader changes. The growing interest in telemedicine in the world’s medical sciences is demonstrated by visibility metrics in Google Scholar, Pubmed, Scopus and Web of Science. National scientific events are assumed to raise interest in the population and influence the creation of general policies. As seen in the example of Poland, the activity of the scientific community gathered around the Polish Telemedicine Society led to novel legal acts that allowed the general practice of telemedicine during the SARS-CoV-2 pandemic. Local scientific conferences focusing on telemedicine research can be a catalyst for changes in attitudes and regulations and the preparation of recommendations for the practice of telemedicine and electronic health. On the basis of the results of this study, it can be concluded that the progress in telemedicine cannot be analyzed in isolation from the ubiquitous developments in technology and telecommunications. More research is needed to assess the cumulative impact of long-standing scientific conferences in telemedicine, as exemplified by the telemedicine and eHealth conferences in Poland.